Noncrystalline highly chlorinated diaryl resin



Dec, 27, 1932. R. L. JENKINS 1,892,398

NONCRYSTALLINE HIGHLY CHLOHINATED DIARYL RESIN Filed Sept. 28, 1929 A.s.T.M, soFTE/wnq PO/NT (l/LOR/NE CONTENT A 607. p/PH ENYL &40Z fl/qh'jolulvq COMPOUND 3= 80% JJIPI'IENYL. & 202 lug/r ,z o/L/Nq (OMPOU/VD c 100% ,D/PHE/YYL Inventor Russell L. Jenkins Patented Dec. 27, 1932 UNITED STATES PATENT OFFICE RUSSELL L. JENKINS, OF ANNISTON, ALABAMA, ASSIGNOR TO SWANH RESEARCH, INC.,

A CORPORATION OF ALABAMA NONGRYSTALLINE HIGHLY CHLORINATED DIABYL RESIN a neauon m September 2a; 1929. Serial No. 895,738.

below 64 C.

It is an object of this invention to pro-- vide a means whereby the higher chlorinated diphenyls may be produced in a permanent, stable, non-crystalline, solid state. It is a further object of this invention to provide a means whereby the higher chlorinated diaryl resins can be produced with a higher softening point than in the case of diphenyl alone. Both of these objects are accomplished by mixing with thediphenyl, before chlorination, various percentages of complex highboiling compounds which are formed as a by-product in the thermal synthesis method of producing diphenyl.

In the accompanying drawing there is shown a graphical illustration of the effect of my invention on the softening point and crystallizing tendency of chlorinated di- 68%, the material which, up to this point has phenyl. The curve marked 40 refers to "I have identified as having the valuable propnousmaterials or A. S. T. method- D The method consists briefly in determining the temperature at which the resin being tested will flow out of a metallic ring inch in diameter and inch thick under the influence of the weight of a small steel ball of specified weight and dimensions and just touch a plate exactly 1 inch below the bottom of the ring. To prepare for the test the resin is castinto the ring in the'molten condition. Heatingof the resin during the test is accomplished by immersing the ring into water which can then be heated at the specified rate. Further details of the test are given in the above publication.

The high-boiling compounds which I hav found it desirable to mix with diphenyl in order to obtain the above results are of a particularly complex nature, and I have not been able to identify them chemically, al-

arating the fraction between 200 and 270 C.,

which comprises the diphenyl fraction. The fraction boiling between 270 and 400 G.

contains the high boiling compounds which erties mentioned above.

' Example I Take a mixture of 80% diphenyl and 20% high boiling compounds, obtained I as described above. Chlorinate this by passing in softening point is considerably below 60 C.,

robably in the neighborhood of 52 C.

en 62% of chlorine hasbeen absorbed,

the softening point has reached a tempera- 5 ture of approximately 61 C. Further chlorination to 65% chlorine results in a softening point in the neighborhood of 81 C. Various other softening points may be obtained in this manner, as desired, by suitably varying the chlorine content.

Ewample I] Take a mixture of 60% diphenyl and 40% diphenyl high boiling compound obtained as described above. Ghlorinate this in the manner described in Example I. When 60% by weight of chlorine has been absorbed, the softening point will be found to' be in the neighborhood of 62 C. On chlorinatingl the mixture further until 62% chlorine has been absorbed, it will be found thatthe softening point has reached a temperature of-72 C.

chlorine content are form .chlorine in high boiling compound Soltenin polntthree ways in which the softening point may be changed. It is, however, obvious that this invention contemplates the use of all possible mixtures of diphenyl and the high boiling compounds or even high boiling compounds alone for the production of the chlorinated product. Instead of mixing the diphenyl and igh boiling compounds beforechlorinating, it is also practical to chlorinate the diphenyl and the diphenyl high. boilin compound.

separately, and then mix them a ter chlorination with equally satisfactory results.

In generahit may be said that an increase in chlorine content of 2% increases the soften- H approximately 10.

' atIcaimis:

- 1. As a new composition of matter a noncrystalline resinous composition essentiall comprised of chlorinated diaryls, said diary lower chlorine content. The softening points which I have obtained and the corresponding given below in tabular.

The examples above described indicate'only having been produced during the thermal synthesis of diphenyl from benzol.

2. As a new composition of matter a noncrystalline composition having a softening point between 60 and 90 C. essentially comprised of chlorinated diaryls, said diaryls having been produced during the thermal synthesis of diphenyl from benzol.

3. As a new composition of matter, achlorinated, non-crystalline diaryl resin consisting of a mixture of chlorinated diaryls, said resins'having a. softening point between 50 and 125 G., and a chlorine content of more than 60 and less than 69 per cent.

4. As a new composition of matter, a chlorinated, non crystalline diaryl resin, consisting of a mixture of chlorinated diphenyl and other complex chlorinated diaryls.

5. As a composition of matter, a chlorinated, non-crystalline diaryl resin, consisting of a mixture of chlorinated diphenyl and other complex chlorinated diaryls, said mixture having a softening point lying between 60 and C.

6. As a new composition of matter, a chlorinated non-crystalline, diaryl resin, consisting of a mixture of chlorinated diphenyl and other complex chlorinated diaryls, said mixture having a softening point lying between 50 and 125 ,C., and a chlorine content ofnore than 60 and less than 69 percent.

7. The

pounds until said mixture has a chlorine content of more than 60%.

rocess of producing chlorinated .non-crysta ine diaryl resins, which comprises chlorinating a mixture of diaryl com- 8'. The process of producing chlorinated f non-crystalline diaryl resins, which comprises chlorinating a mixture of diaryl compounds in the presence of iron as a chlorination catalyst.

9. The process of producin chlorinated non-crystalline diaryl resins, which comprises chlo'rinating a mixture of diaryl compounds in the presence ofiron as a chlorination catalyst until said mixture has a chlorine content of more than 60%.

10. The rocess of producing chlorinated non-crysta line diaryl resins, whlch comprises mixing diphenyl with those com lex h boiling diaryl compounds formed uring t e diphen 1 synthesis operation and chlormating sai mlxture-toa' predetermined chlorine content. 1

11. The process of producing non-crystalline-chlorinated diphenyl containing resins comprisin chlorinating a mixture of diphenyl an other diaryls to a predetermined content such that a 2% increase in the latter 9 property results in a 10 C. increase-in th ormer property. I i

13. As a new composition of matter a. series of chlorinated diaryl resins containin chlorinated diphenyl and having a relation between softening point and chlorine content such that a 2% increase in the latter property results in a, 10 C. increase in the former property. y

In testimony whereof I aifix my si ature.

RUSSELL L. JE NS. 

